Sodium Carbonate → 6-Bromo-2-(9-phenanthrenyl)naphthalene

HRID 1662910Notes

Reaction equation

HRID 1662910 reaction equation
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24](Br)[CH:25]=2)[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(COC)OC>[Br:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([C:12]1[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:23]=[CH:22]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6405912,6-DibromonaphthaleneHCID 117757049-Phenanthracenylboronic acid

Product 1

HCID 575398276-Bromo-2-(9-phenanthrenyl)naphthaleneYield 29.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
78 °C

Procedure

Under an argon gas atmosphere, 19.41 g (87.4 mmol) of 9-phenanthreneboronic acid, 25.00 g (87.4 mmol) of 2,6-dibromonaphthalene, 2.02 g (1.75 mmol) of tetrakis(triphenylphosphine) palladium(0), 400 mL of dimethoxyethane and 132 mL of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 78 degrees C. The reaction mixture experienced filtration, filtrate thereof was cleansed with water and the reaction mixture was dried with magnesium sulfate. Then, toluene was distilled away under reduced pressure. By refining residue thereof by silica-gel column chromatography and by recrystallizing the residue by acetic ether, 9.80 g of 6-bromo-2-(9-phenanthrenyl)naphthalene was obtained with an yield of 29%.

Workup

  1. filtrationfiltration, filtrate
  2. dry with materialthe reaction mixture was dried with magnesium sulfate
  3. distillationThen, toluene was distilled away under reduced pressure
  4. customby silica-gel column chromatography and by recrystallizing the residue by acetic ether

Sources & evidence

ORD record
ord-d8fc4368d0124fecbe6db0db7db10da4
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

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